Benzenesulfonyl chloride → HCID 10446995, compound

HRID 1373236Notes

Reaction equation

HRID 1373236 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].S([O-])(O)(=O)=O.[K+]>O1CCCC1.C(O)C.O.CN(C)C(=O)C>[C:14]1([S:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 516920Potassium bisulfate

Product 1

HCID 10446995HCID 10446995, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of ethyl 4-aminophenylacetate (3.0 g, 17 mmols), benzenesulfonyl chloride (3.0 g, 17 mmols) and N,N-dimethylacetamide (30 ml) was stirred at room temperature for 2 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure. A 1 N sodium hydroxide solution (50 ml, 50 mmols) was added to a solution of the residue in tetrahydrofuran (50 ml) and ethanol (50 ml). The resulting mixture was stirred at 60° C. for 1 hour. Water was added to the reaction mixture, which was acidified with potassium hydrogensulfate added thereto, and then extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was crystallized from hexane/ethyl acetate to give a solid of 4-benzenesulfonylaminophenylacetic acid (3.1 g, 64%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. stirringThe resulting mixture was stirred at 60° C. for 1 hour
  7. additionadded
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water
  10. dry with materialdried with anhydrous magnesium sulfate
  11. concentrationThis was concentrated under reduced pressure
  12. customthe residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1cdcd17e7861439286d06d9e4b8674ff
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

Loading…